Water → N-{2-[4-Fluoro-2-(2-{4-[(1-phenylpyrrolidin-3(S)-yloxy)phenyl]piperidin-3-yloxy}ethoxy)phenyl]ethyl}acetamide

HRID 1176573Notes

Reaction equation

HRID 1176573 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][C:7]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:8]=1[O:9][CH2:10][CH2:11][O:12][CH:13]1[CH:18]([C:19]2[CH:24]=[CH:23][C:22](O)=[CH:21][CH:20]=2)[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]1)(=[O:3])[CH3:2].[C:38](=[O:41])([O-])O.[Na+].ClC(OC[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=O.O>C(OCC)(=O)C>[F:37][C:34]1[CH:35]=[CH:36][C:7]([CH2:6][CH2:5][NH:4][C:1](=[O:3])[CH3:2])=[C:8]([O:9][CH2:10][CH2:11][O:12][CH:13]2[CH:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[O:41][C@H:38]3[CH2:2][CH2:1][N:4]([C:48]4[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=4)[CH2:5]3)[CH2:17][CH2:16][NH:15][CH2:14]2)[CH:33]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 68504580HCID 68504580, compound

Product 1

HCID 68497210N-{2-[4-Fluoro-2-(2-{4-[(1-phenylpyrrolidin-3(S)-yloxy)phenyl]piperidin-3-yloxy}ethoxy)phenyl]ethyl}acetamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Analogously to Method A, 2.90 g of tert-butyl 3-{2-[2-(2-acetylaminoethyl)-5-fluorophenoxy]ethoxy}-4-(4-hydroxyphenyl)piperidine-1-carboxylate (Example 223) are reacted. The resulting crude product is subsequently taken up in 50 ml each of ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The reaction mixture is cooled in an ice bath and admixed with 1.00 ml of benzyl chloroformate and subsequently stirred at 0° C. for a further 30 minutes. The reaction mixture is admixed with 300 ml of water and extracted with ethyl acetate (2×250 ml). The combined organic phases are dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is used further as the crude product. Rf=0.30 (EtOAc); Rt=4.33

Workup

  1. temperatureThe reaction mixture is cooled in an ice bath
  2. extractionextracted with ethyl acetate (2×250 ml)
  3. dry with materialThe combined organic phases are dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-bee6f5bfe740466bbbdc6de1f9207295
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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